Benzenamine, 3-chloro-, hydrochloride (1:1) → 4-(3-chloro-phenylamino)-3-(morpholin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068888

Reaktionsgleichung

Reaktionsgleichung von HRID 1068888
[N:1]1([C:7]2[C:11]([C:12]#[N:13])=[C:10]([N:14]=[CH:15][N:16](C)C)[NH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)N>CO>[Cl:20][C:21]1[CH:27]=[C:26]([NH:13][C:12]2[N:16]=[CH:15][N:14]=[C:10]3[NH:9][N:8]=[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[C:11]=23)[CH:25]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 54020168N'-[3-(morpholin-4-yl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethyl-formamidine

Produkt 1

HCID 211906484-(3-chloro-phenylamino)-3-(morpholin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

With the exclusion of air, 1.86 g (7.49 mmol) of N′-[3-(morpholin-4-yl)-4-cyano-1 H-pyrazol-5-yl]-N,N-dimethyl-formamidine in 45 ml of methanol are heated to boiling with 1.84 g (11.2 mmol) of 3-chloro-aniline hydrochloride, during which the solid temporarily dissolves. After about 30 min, a precipitate separates out again. After 8 hours the reaction mixture is cooled, filtered and washed with methanol and DIPE. Stirring the crude product in a boiling mixture of 40 ml of ethanol, 20 ml of chloroform and 20 ml of dioxane yields 4-(3-chloro-phenylamino)-3-(morpholin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 275-276° C.; HPLC:tRet(grad20-100/20)=11.6.

Aufarbeitung

  1. dissolutiontemporarily dissolves
  2. temperatureAfter 8 hours the reaction mixture is cooled
  3. filtrationfiltered
  4. washwashed with methanol and DIPE
  5. additionin a boiling mixture of 40 ml of ethanol, 20 ml of chloroform and 20 ml of dioxane

Quellen und Nachweise

ORD-Eintrag
ord-728f40be02294077b9b650e3d6f24546
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251911B1

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